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The strategy of making an experience so onerous that users will go to some lengths (paying money, choosing different travel dates, etc.) to avoid it. From Tim Wu in an article on airline fees from the New Yorker (link )
Tim Wu Quotation

But the fee model comes with systematic costs that are not immediately obvious. Here’s the thing: in order for fees to work, there needs be something worth paying to avoid. That necessitates, at some level, a strategy that can be described as “calculated misery.” Basic service, without fees, must be sufficiently degraded in order to make people want to pay to escape it. And that’s where the suffering begins.

I suspect many student view what are sometimes referred to as weed-out courses (calculus for engineers, organic chemistry for pre-med) as a sort of calculated misery. This class is so hard that I'll change my major rather than take it.

Larry Ferlazzo has pointed out how charter schools can be seen as an instance of calculated misery. Systematic defunding of public schools create an environment where parents and the broader community will accept charters, despite their for profit nature and corporateness, because they are desperate to escape decaying public schools.

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